ChemicalBook--->CAS DataBase List--->356-12-7

356-12-7

356-12-7 Structure

356-12-7 Structure
IdentificationBack Directory
[Name]

Fluocinonide
[CAS]

356-12-7
[Synonyms]

Vanos
Lidex
Topsyn
Lonide
topsym
lidexe
metosyn
Gelisyn
Lidemol
Topsyne
flucinar
Biscosal
Straderm
Topsymin
Cortalar
NSC 101791
Flucetonide
FLUOCINOMIDE
FLUOCINONIDE
fluocinolide
Fluocinonide RS
Fluoxetine acetate
Fluocinonideacetate
fluocinolideacetate
Fluocinonide(Vanos)
Fluorocarbon acetate
Fluocinonide (100 mg)
Fluocinoide acetonide
Fluocinonide Acetonide
Fluocinonide USP/EP/BP
Fluocinonide, Micronized
FLUOCINONIDE,MICRONIZED,USP
fluocinoloneacetonideacetate
Fluocinonide Solution, 100ppm
FLUOCINONIDE ACETONIDE 21-ACETATE
FLUOCINOLONE ACETONIDE 21-ACETATE
2-chloroethoxy(diphenyl)phosphine
Fluocinolone Acetonide EP Impurity M
droxy-,cyclic17-acetalwithacetone,21-acetate
pregna-1,4-diene-3,20-dione,6-alpha,9-difluoro-11-beta,16-alpha,17,21-tetrahy
Fluocinolone Acetonide Impurity 13 (Fluocinolone Acetonide EP Impurity M)(Fluocinonide)
1,4-PREGNADIEN-6-ALPHA, 9-ALPHA-DIFLUORO-11-BETA, 16-ALPHA, 17,21-TETROL-3,20-DIONE 16,17-ACETONIDE 21-ACETATE
(6α,11β,16α)-21-(Acetyloxy)-6,9-difluoro-11-hydroxy-16,17-[(1-Methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione
Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-6,9-difluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]-, (6α,11β,16α)-
Pregna-1,4-diene-3,20-dione, 6α,9-difluoro-11β,16α,17,21-tetrahydroxy-, cyclic 16,17-acetal with acetone, 21-acetate (7CI, 8CI)
pregna-1,4-diene-3,20-dione, 6-alpha, 9-difluoro-11-beta,16-alpha,17,21-tetrahy droxy-, cyclic 17-acetal with acetone, 21-acetate flucinar fluocinolide fluocinolide acetate fluocinolone acetonide 21-acetate fluocinolone acetonide acetate fluocinonide lidex e Fluocinonide acetate 21-Acatyloxy-6,9-diflulro-11-hydroxy-16,17-[(1-methyl-ethylidene)bis(oxy)]pregna-1,4-di-ene-3,20-dione
[EINECS(EC#)]

206-597-6
[Molecular Formula]

C26H32F2O7
[MDL Number]

MFCD00079302
[MOL File]

356-12-7.mol
[Molecular Weight]

494.52
Chemical PropertiesBack Directory
[Melting point ]

309 °C
[alpha ]

D +83° (chloroform)
[Boiling point ]

235°C (rough estimate)
[density ]

1.2001 (estimate)
[storage temp. ]

Refrigerator
[solubility ]

DMSO: ≥19mg/mL
[form ]

powder
[pka]

12.77±0.70(Predicted)
[color ]

white to tan
[Optical Rotation]

[α]/D +75 to +90°, c = 1 in dichloromethane
[Water Solubility ]

0.53mg/L(25 ºC)
[Major Application]

pharmaceutical (small molecule)
[InChIKey]

WJOHZNCJWYWUJD-IUGZLZTKSA-N
[SMILES]

[C@@]12(C(=O)COC(=O)C)OC(C)(C)O[C@@H]1C[C@@]1([H])[C@]3([H])C[C@@H](C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]21C)F |&1:0,13,15,17,20,27,29,31,34,r|
Safety DataBack Directory
[Symbol(GHS) ]

Skull and Crossbones (GHS06)Health Hazard (GHS08)
GHS06,GHS08
[Signal word ]

Danger
[Hazard statements ]

H300-H361
[Precautionary statements ]

P201-P301+P310+P330
[Hazard Codes ]

T+
[Risk Statements ]

28-63
[Safety Statements ]

22-25-28-36/37/39-45
[RIDADR ]

UN 2811 6.1/PG 2
[WGK Germany ]

3
[RTECS ]

TU3831000
[HazardClass ]

6.1(a)
[PackingGroup ]

I
[HS Code ]

2937220000
[Storage Class]

6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials
[Hazard Classifications]

Acute Tox. 2 Oral
Repr. 2
[Toxicity]

guinea pig,LD50,subcutaneous,> 3170mg/kg (3170mg/kg),Drugs in Japan Vol. 6, Pg. 694, 1982.
Hazard InformationBack Directory
[Chemical Properties]

White Solid
[Originator]

Topsyn ,Recordati,Italy,1970
[Uses]

antiinflammatory, glucocorticoid
[Uses]

Glucocorticoid; anti-inflammatory.
[Definition]

ChEBI: Fluocinonide is an organic molecular entity.
[Indications]

Fluocinonide (Lidex, Lidex E, Fluonex) is a synthetic fluorinated corticosteroid.
[Manufacturing Process]

To a suspension of 500 mg of 6α-fluoro-triamcinolone in 75 ml of acetone is added 0.05 milliliters of 72% perchloric acid and the mixture agitated-at room temperature for 3 hours. During this period the crystals gradually dissolve and the clear solution is neutralized with dilute bicarbonate and the acetone removed in vacuo. The resulting crystalline suspension is filtered and the crystals washed with water. The dried material is recrystallized from 95% alcohol to give the pure acetonide.
A solution of 50 mg of 6α-fluoro-triamcinolone acetonide in 1 ml of pyridine and 1 ml of acetic anhydride is allowed to stand at room temperature for 18 hours. Removal of the reagents in vacuo gives a crystalline residue which after crystallization from acetone-hexane gives the pure 16α,17α- isopropylidene 6α-fluoro-triamcinolone 21 acetate (fluocinonide), as described in US Patent 3,197,469.
[Brand name]

Lidex (Medicis); Vanos (Medicis).
[Therapeutic Function]

Antiinflammatory, Glucocorticoid
[Biochem/physiol Actions]

Flucinonide is a fluorinated glucocorticid that is used as a topical anti-inflammatory agent. Recently, flucinonide and other fluorinated glucocorticolids were identified as smoothend agonists. Flucinonide induces expression of Gli-reporter luciferase in Shh-LIGHT2 cells.
[References]

[1] Chemistry Letters, 2018, vol. 47, # 1, p. 110 - 112
[2] Patent: CN107619426, 2018, A. Location in patent: Paragraph 0008; 0140-0146
Spectrum DetailBack Directory
[Spectrum Detail]

Fluocinonide(356-12-7)1HNMR
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